Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition

This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis...

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Published in:Journal of the American Chemical Society 1996-07, Vol.118 (29), p.6826-6840
Main Authors: Lin, Chun-Cheng, Shimazaki, Makoto, Heck, Marie-Pierre, Aoki, Shin, Wang, Ruo, Kimura, Teiji, Ritzèn, Helena, Takayama, Shuichi, Wu, Shih-Hsiung, Weitz-Schmidt, Gabriel, Wong, Chi-Huey
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cited_by cdi_FETCH-LOGICAL-a361t-aa98c534876f25dba7fa99830223d59350cbfdfda842e9bd8a1f788cd7fbdcf53
cites cdi_FETCH-LOGICAL-a361t-aa98c534876f25dba7fa99830223d59350cbfdfda842e9bd8a1f788cd7fbdcf53
container_end_page 6840
container_issue 29
container_start_page 6826
container_title Journal of the American Chemical Society
container_volume 118
creator Lin, Chun-Cheng
Shimazaki, Makoto
Heck, Marie-Pierre
Aoki, Shin
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Wu, Shih-Hsiung
Weitz-Schmidt, Gabriel
Wong, Chi-Huey
description This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Lex), Lewis Y (Ley), glycopeptides, and sialyl Lewis X (SLex) mimetics. Both α-O-fucosyl-l-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLex mimetics, and some fucopeptides prepared were 5−10 times more active than SLex as inhibitors of E-selectin.
doi_str_mv 10.1021/ja952265x
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title Synthesis of Sialyl Lewis X Mimetics and Related Structures Using the Glycosyl Phosphite Methodology and Evaluation of E-Selectin Inhibition
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